The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes

I. D. Kalikhman; V. A. Pestunovich; B. A. Gostevskii; O. B. Bannikova; M. G. Voronkov

doi:10.1016/0022-328X(88)80499-6

The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes

I. D. Kalikhman, V. A. Pestunovich, B. A. Gostevskii, O. B. Bannikova, M. G. Voronkov

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

Pentacoordinate silicon compounds containing a "chelate" six-membered silacarbofunctional ring, such as the chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]-dimethylsilanes, Me₂ClSiCH₂NMe₂NC(O)R with R = CF₃ (Ib), C₆H₅ (Ic), 4′-MeC₆H₄ (Id), 4′-MeOC₆H₄ (Ie), 4′-NO₂C₆H₄ (If) have been synthesized for the first time and were studied by NMR spectroscopy. In contrast to Ib in molecules of Ia (R = Me), IcIf the ClSi bond rather than OSi bond is the weaker component of the hypervalent OSiCl bond, which implies the possibility of Cl → Si coordinative interaction. An irreversible rearrangement of compounds I upon heating leads to (OSi)chloro[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes, Me₂ClSiCH₂-N[C(O)R]NMe₂ (II), and was used for preparative purposes.

Original language	English
Pages (from-to)	169-180
Number of pages	12
Journal	Journal of Organometallic Chemistry
Volume	338
Issue number	2
DOIs	https://doi.org/10.1016/0022-328X(88)80499-6
State	Published - 12 Jan 1988
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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Kalikhman, I. D., Pestunovich, V. A., Gostevskii, B. A., Bannikova, O. B., & Voronkov, M. G. (1988). The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes. Journal of Organometallic Chemistry, 338(2), 169-180. https://doi.org/10.1016/0022-328X(88)80499-6

Kalikhman, I. D. ; Pestunovich, V. A. ; Gostevskii, B. A. et al. / The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes. In: Journal of Organometallic Chemistry. 1988 ; Vol. 338, No. 2. pp. 169-180.

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title = "The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes",

abstract = "Pentacoordinate silicon compounds containing a {"}chelate{"} six-membered silacarbofunctional ring, such as the chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]-dimethylsilanes, Me2ClSiCH2NMe2NC(O)R with R = CF3 (Ib), C6H5 (Ic), 4′-MeC6H4 (Id), 4′-MeOC6H4 (Ie), 4′-NO2C6H4 (If) have been synthesized for the first time and were studied by NMR spectroscopy. In contrast to Ib in molecules of Ia (R = Me), IcIf the ClSi bond rather than OSi bond is the weaker component of the hypervalent OSiCl bond, which implies the possibility of Cl → Si coordinative interaction. An irreversible rearrangement of compounds I upon heating leads to (OSi)chloro[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes, Me2ClSiCH2-N[C(O)R]NMe2 (II), and was used for preparative purposes.",

author = "Kalikhman, {I. D.} and Pestunovich, {V. A.} and Gostevskii, {B. A.} and Bannikova, {O. B.} and Voronkov, {M. G.}",

year = "1988",

month = jan,

day = "12",

doi = "10.1016/0022-328X(88)80499-6",

language = "English",

volume = "338",

pages = "169--180",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

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Kalikhman, ID, Pestunovich, VA, Gostevskii, BA, Bannikova, OB & Voronkov, MG 1988, 'The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes', Journal of Organometallic Chemistry, vol. 338, no. 2, pp. 169-180. https://doi.org/10.1016/0022-328X(88)80499-6

The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes. / Kalikhman, I. D.; Pestunovich, V. A.; Gostevskii, B. A. et al.
In: Journal of Organometallic Chemistry, Vol. 338, No. 2, 12.01.1988, p. 169-180.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes

AU - Kalikhman, I. D.

AU - Pestunovich, V. A.

AU - Gostevskii, B. A.

AU - Bannikova, O. B.

AU - Voronkov, M. G.

PY - 1988/1/12

Y1 - 1988/1/12

N2 - Pentacoordinate silicon compounds containing a "chelate" six-membered silacarbofunctional ring, such as the chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]-dimethylsilanes, Me2ClSiCH2NMe2NC(O)R with R = CF3 (Ib), C6H5 (Ic), 4′-MeC6H4 (Id), 4′-MeOC6H4 (Ie), 4′-NO2C6H4 (If) have been synthesized for the first time and were studied by NMR spectroscopy. In contrast to Ib in molecules of Ia (R = Me), IcIf the ClSi bond rather than OSi bond is the weaker component of the hypervalent OSiCl bond, which implies the possibility of Cl → Si coordinative interaction. An irreversible rearrangement of compounds I upon heating leads to (OSi)chloro[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes, Me2ClSiCH2-N[C(O)R]NMe2 (II), and was used for preparative purposes.

AB - Pentacoordinate silicon compounds containing a "chelate" six-membered silacarbofunctional ring, such as the chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]-dimethylsilanes, Me2ClSiCH2NMe2NC(O)R with R = CF3 (Ib), C6H5 (Ic), 4′-MeC6H4 (Id), 4′-MeOC6H4 (Ie), 4′-NO2C6H4 (If) have been synthesized for the first time and were studied by NMR spectroscopy. In contrast to Ib in molecules of Ia (R = Me), IcIf the ClSi bond rather than OSi bond is the weaker component of the hypervalent OSiCl bond, which implies the possibility of Cl → Si coordinative interaction. An irreversible rearrangement of compounds I upon heating leads to (OSi)chloro[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes, Me2ClSiCH2-N[C(O)R]NMe2 (II), and was used for preparative purposes.

UR - http://www.scopus.com/inward/record.url?scp=0001699344&partnerID=8YFLogxK

U2 - 10.1016/0022-328X(88)80499-6

DO - 10.1016/0022-328X(88)80499-6

M3 - Article

AN - SCOPUS:0001699344

SN - 0022-328X

VL - 338

SP - 169

EP - 180

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 2

ER -

Kalikhman ID, Pestunovich VA, Gostevskii BA, Bannikova OB, Voronkov MG. The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes. Journal of Organometallic Chemistry. 1988 Jan 12;338(2):169-180. doi: 10.1016/0022-328X(88)80499-6

The synthesis and NMR spectra of new pentacoordinate silicon compounds, (OSi)- and (ClSi)-chloro[1-(1,1-dimethyl-2-acylhydrazonium)methyl]dimethylsilanes and (OSi)chloro-[2-(1,1-dimethyl-2-acylhydrazino)methyl]dimethylsilanes

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